Recently Listed Open House 5/31 1pm - 3pm
3 Winding Trail 3
Middlebury, CT, 06762 $ 559,900
Bedrooms3 Baths2.1 Sq 3,179 Monthly Estimate*
$ 3,447
for $559,900 with 3 bedrooms and 2 full baths, 1 half bath. This 3,179 square foot condo was built in 2007.
Welcome to 3 Winding Trail, nestled on a quiet cul-de-sac in the highly desirable Ridgewood community of Middlebury. This beautifully maintained 3-bedroom, 2.5-bath condo offers the perfect blend of elegance, comfort, and low-maintenance living across 4 finished levels, including a sun-filled walk-out lower level. From the moment you step inside, you'll appreciate the gleaming hardwood floors, natural light throughout, spacious layout, and updated kitchen featuring granite countertops, stainless steel appliances, and ample space for entertaining. The spacious primary suite offers a peaceful retreat, while the additional finished spaces provide incredible flexibility for a family room, home office, gym, playroom, or guest area. Step outside to your private deck and patio surrounded by peaceful wooded views - perfect for relaxing or entertaining. Enjoy resort-style amenities including a pool, tennis courts, clubhouse, and fitness center, all within minutes of shopping, dining, and major commuter routes. Move-in ready and located in one of Middlebury's most sought-after communities, this is a rare opportunity you won't want to miss.
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Open House
5/31/2026 1:00 PM - 3:00 PM
3 Winding Trail 3 Middlebury, CT
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm
FeaturesGeneralZoning Residential
Neighborhood N/A
County New Haven
Unit Number 3
Tax Year July 2025-June 2026
Property Type Condo/Co-Op For Sale
Status Active
Directions GPS-friendly
High School Per Board of Ed
City Middlebury
Elementary School Per Board of Ed
Sq Ft Total 3179
DOM 5
Year Built 2007
Complex Ridgewood at Middlebury
Style Townhouse
Year Built Source Public Records
Pool Description In Ground Pool
Association Fee Includes Club House Tennis Grounds Maintenance Trash Pickup Snow Removal Pest Control Pool Service Road Maintenance
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InteriorCooling System Central Air
Total Number of Units 141
Total Rooms 7
Basement Description Full Full With Walk-Out
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ExteriorWater Source Public Water Connected
Lot Description On Cul-De-Sac
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* Excluded FeaturesList ByShowcase Realty, Inc.Broker
mayra@showcasect.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $3,447
- Monthly Property Taxes
- $670
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbyCondo listings in Middlebury, CT
Average List Price $572,655
Percent of Sale Price 2%
About Middlebury, CT 7,671 Population
18% Since 2002
$ 105,125 Median Income
46.66 Median Age
27% Households with Children
Trends Information provided by ATTOM Data Solutions.
3092524 Elementary School
1232933 Middle School
Per Board of Ed High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 5/23/2026 | $559,900 | | Listed Price |